Substituted thienyl(amino)sulphonylureas

ABSTRACT

The invention relates to novel substituted thienyl(amino)sulphonylureas of the general formula (I) 
                         
in which A, Q, R 1 , R 2 , R 3 , R 4  and R 5  are each as defined in the description, to processes for their preparation and to their use as herbicides.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a divisional of U.S. patent application Ser. No.10/049,747, filed Jan. 31, 2002 (now U.S. Pat. No. 6,887,831), which isa 35 U.S.C. §371 national stage of PCT/EP00/07096, filed Jul. 25, 2000.

The invention relates to novel substituted thienyl(amino)sulphonylureas,to processes for their preparation and to their use as herbicides.

It is already known that certain substituted thienylsulphonylureas haveherbicidal properties (cf. EP-A-30142/U.S. Pat. No. 4,481,029/U.S. Pat.No. 4,599,103/U.S. Pat. No. 4,701,535, EP-A-97122/U.S. Pat. No.4,549,898, EP-A-207609/U.S. Pat. No. 4,668,281). However, the herbicidalactivity of these known compounds is not entirely satisfactory.

This invention, accordingly, provides the novel substitutedthienyl(amino)sulphonylureas of the general formula (I)

in which

-   A represents nitrogen or a CH grouping,-   Q represents a single bond or represents NH,-   R¹ represents hydrogen, halogen or in each case optionally    substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino,    aryloxy or heterocyclyloxy,-   R² represents hydrogen, halogen or in each case optionally    substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino,    aryloxy or heterocyclyloxy,-   R³ represents hydrogen or optionally substituted alkyl,-   R⁴ represents halogen or optionally substituted alkyl and—if Q    represents NH—also represents hydrogen, and-   R⁵ represents hydrogen or in each case optionally substituted alkyl,    alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl or heterocyclyl,    and salts of compounds of the formula (I).

Saturated or unsaturated hydrocarbon groupings, such as alkyl, alkenylor alkinyl, are in each case straight-chain or branched as far as thisis possible—including in combination with hetero atoms, such as inalkoxy.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitution the substituents can be identical ordifferent.

Preferred substituents or ranges of the radicals which are present inthe formulae given above and below are defined below.

-   A preferably represents nitrogen or a CH grouping.-   Q preferably represents a single bond or represents NH.-   R¹ preferably represents hydrogen, represents halogen, represents in    each case optionally cyano-, halogen- or C₁–C₄-alkoxy-substituted    alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each    case 1 to 4 carbon atoms in the alkyl groups, or represents in each    case optionally cyano-, halogen-, C₁–C₄-alkyl- or    C₁–C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or    tetrahydrofuryloxy.-   R² preferably represents hydrogen, represents halogen, represents in    each case optionally cyano-, halogen- or C₁–C₄-alkoxy-substituted    alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each    case 1 to 4 carbon atoms in the alkyl groups, or represents in each    case optionally cyano-, halogen-, C₁–C₄-alkyl- or    C₁–C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or    tetrahydrofuryloxy.-   R³ preferably represents hydrogen or represents optionally    C₁–C₄-alkoxy-, C₁–C₄-alkyl-carbonyl- or    C₁–C₄-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms.-   R⁴ preferably represents optionally cyano-, halogen- or    C₁–C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms and—if Q    represents NH—also represents hydrogen.-   R⁵ preferably represents hydrogen, represents optionally cyano-,    halogen- or C₁–C₄-alkoxy-substituted alkyl having 1 to 6 carbon    atoms, represents in each case optionally halogen-substituted    alkenyl or alkinyl having in each case 2 to 6 carbon atoms,    represents in each case optionally cyano-, halogen- or    C₁–C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each    case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1    to 4 carbon atoms in the alkyl moiety, or represents in each case    optionally cyano-, halogen-, C₁–C₄-alkyl- or    C₁–C₄-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl.-   A particularly preferably represents nitrogen or a CH grouping.-   Q particularly preferably represents a single bond or represents NH.-   R¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, or represents in each case optionally cyano-,    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio,    ethylthio, n- or i-propylthio, methyl-amino, ethylamino, n- or    i-propylamino, dimethylamino or diethylamino.-   R² particularly preferably represents fluorine, chlorine, bromine,    or represents in each case optionally cyano-, fluorine-, chlorine-,    methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,    methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or    i-propylthio, methylamino, ethylamino, n- or i-propylamino,    dimethylamino or diethylamino.-   R³ particularly preferably represents hydrogen or represents in each    case optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-,    propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n-    or i-propoxycarbonyl-substituted methyl or ethyl.-   R⁴ particularly preferably represents in each case optionally    cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl.-   R⁵ particularly preferably represents hydrogen, represents in each    case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-    or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, represents in each case optionally fluorine-, chlorine-    or bromine-substituted propenyl, butenyl, propinyl or butinyl, or    represents in each case optionally cyano-, fluorine-, chlorine-,    bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl,    cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.-   A very particularly preferably represents nitrogen or a CH grouping.-   Q very particularly preferably represents a single bond or    represents NH.-   R¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, represents in each case optionally fluorine-,    chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy,    ethoxy, methylthio, ethylthio, methyl-amino, ethylamino, or    represents dimethylamino.-   R² very particularly preferably represents fluorine, chlorine,    bromine, represents in each case optionally fluorine-, chlorine-,    methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy,    methylthio, ethylthio, methylamino or ethylamino, or represents    dimethylamino.-   R³ very particularly preferably represents hydrogen or methyl.-   R⁴ very particularly preferably represents in each case optionally    fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl.-   R⁵ very particularly preferably represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl, or represents in each case optionally fluorine- or    chlorine-substituted propenyl or propinyl.-   A most preferably represents a CH grouping.-   R¹ and R² most preferably represent methoxy.-   R³ most preferably represents hydrogen.

The invention also preferably provides the sodium, potassium, magnesium,calcium, ammonium, C₁–C₄-alkyl-ammonium, di-(C₁–C₄-alkyl)-ammonium,tri-(C₁–C₄-alkyl)-ammonium, tetra-(C₁–C₄-alkyl)-ammonium,tri-(C₁–C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium- anddi-(C₁–C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I),in which A, Q, R¹, R², R³, R⁴ and R⁵ have the meaning given above asbeing preferred.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given ranges ofpreferred compounds.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the meanings given above asbeing preferred.

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningsgiven above as being very particularly preferred.

Most preference according to the invention is given to the compounds inwhich R¹, R², R³ or A have one of the meanings given as being mostpreferred.

Examples of the compounds of the formula (I) according to the inventionare listed in the groups below.

Group 1

Here, A, Q, R¹, R² and R³ have, for example, the meanings listed below:

A Q R¹ R² R³ CH — OCH₃ OCH₃ H CH NH OCH₃ OCH₃ H CH — CH₃ OCH₃ H CH NHCH₃ OCH₃ H CH CH₃ CH₃ H CH NH CH₃ CH₃ H CH — Cl OCH₃ H CH — H CH₃ H N —CH₃ OCH₃ CH₃ N — OCH₃ OCH₃ CH₃ N — CH₃ OCH₃ H N NH CH₃ OCH₃ H N — OCH₃OCH₃ H N NH OCH₃ OCH₃ H N — CH₃ CH₃ H N — OCHF₂ N(CH₃)₂ H N — CH₃ SCH₃ HN — C₂H₅ OCH₃ H N — CH₃ OC₂H₅ H N — H OCH₃ H N — OCH₃

H N — CH₃ N(CH₃)₂ H CH — OCH₃

H CH — CH₃

H CH — Cl

H N — H

H N — N(CH₃)₂ OCH₂CF₃ HGroup 2

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 3

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 4

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 5

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 6

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 7

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 8

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 9

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 10

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 11

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 12

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 13

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 14

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 15

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 16

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 17

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 18

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 19

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 20

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 21

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 22

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 23

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 24

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

Group 25

Here, A, Q, R¹, R² and R³ have, for example, the meaning given above inGroup 1.

The novel substituted thienyl(amino)sulphonylureas of the generalformula (I) have strong herbicidal activity.

The novel substituted thienyl(amino)sulphonylureas of the generalformula (I) are obtained when

(a) Aminoazines of the General Formula (II)

in which

-   A, R¹ and R² are each as defined above-   are reacted with thienyl(amino)sulphonyl isocyanates of the general    formula (III)

in which

-   Q, R⁴ and R⁵ are each as defined above,-   if appropriate in the presence of a reaction auxiliary and if    appropriate in the presence of a diluent,    or when    (b) Substituted Aminoazines of the General Formula (IV)

in which

-   A, R¹ and R² are each as defined above,-   Z represents halogen, alkoxy or aryloxy and-   R has the meaning given above for R³ or represents the grouping    —C(O)—Z,-   are reacted with thiophene derivatives of the general formula (V)

in which

-   Q, R⁴ and R⁵ are each as defined above,-   if appropriate in the presence of a reaction auxiliary and if    appropriate in the presence of a diluent,    or when    (c) Aminoazines of the General Formula (II)

in which

-   A, R¹ and R² are each as defined above,-   are reacted with thiophene derivatives of the general formula (VI)

in which

-   Q, R⁴ and R⁵ are each as defined above and-   Z represents halogen, alkoxy or aryloxy,-   if appropriate in the presence of a reaction auxiliary and if    appropriate in the presence of a diluent,    or when    (d) Aminoazines of the General Formula (II)

in which

-   A, R¹ and R² are each as defined above,-   are reacted with chlorosulphonyl isocyanate, if appropriate in the    presence of a diluent, and the resulting    chlorosulphonylaminocarbonylamino-azines of the general formula    (VII)

in which

-   A, R¹ and R² are each as defined above-   are—after intermediate isolation or “in situ”—-   reacted with substituted aminothiophenes of the general formula    (VIII)

in which

-   R⁴ and R⁵ are each as defined above,-   if appropriate in the presence of a reaction auxiliary and if    appropriate in the presence of a diluent,    and the compounds of the formula (I) obtained by process (a),    (b), (c) or (d) are, if appropriate, converted by customary methods    into salts.

Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and4-ethoxycarbonyl-2-trifluoromethyl-thien-3-yl-sulphonyl isocyanate asstarting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following formulascheme:

Using, for example,2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and2-ethyl-4-i-propoxycarbonyl-thiophene-3-sulphonamide as startingmaterials, the course of the reaction in the process (b) according tothe invention can be illustrated by the following formula scheme:

Using, for example, 2-amino-4-chloro-6-methoxy-pyrimidine and O-phenylN-(4-ethoxycarbonyl-2-methyl-thien-3-yl-sulphonyl)-urethane as startingmaterials, the course of the reaction in the process (c) according tothe invention can be illustrated by the following formula scheme:

Using, for example, 2-amino-4-methoxy-6-trifluoromethyl-pyrimidine,chloro-sulphonyl isocyanate and ethyl3-amino-2-ethyl-thiophene-4-carboxylate as starting materials, thecourse of the reaction in the process (d) according to the invention canbe illustrated by the following formula scheme:

The formula (II) provides a general definition of the aminoazines to beused as starting materials in the processes (a), (c) and (d) accordingto the invention for preparing the compounds of the general formula (I).In the formula (II), A, R¹ and R² each preferably or in particular havethose meanings which have already been mentioned above, in connectionwith the description of the compounds of the formula (I), as beingpreferred or as being particularly preferred for A, R¹ and R².

The aminoazines of the formula (II) are known chemicals for synthesis,some of which are commercially available.

The formula (III) provides a general definition of thethienyl(amino)sulfonyl isocyanates further to be used as startingmaterials in the process (a) according to the invention. In the formula(III), Q, R⁴ and R⁵ each preferably or in particular have those meaningswhich have already been mentioned above, in connection with thedescription of the compounds of the formula (I), as being preferred oras being particularly preferred for Q, R⁴ and R⁵.

The starting materials of the formula (III) are known and/or can beprepared by processes known per se (cf. EP 30142/U.S. Pat. No.4,481,029/U.S. Pat. No. 4,599,103/U.S. Pat. No. 4,701,535).

The thienyl(amino)sulphonyl isocyanates of the formula (III) areobtained when thiophene derivatives of the general formula (V)—above—arereacted with phosgene or thiophosgene, if appropriate in the presence ofan alkyl isocyanate, such as, for example, butyl isocyanate, ifappropriate in the presence of a reaction auxiliary, such as, forexample, diazabicyclo[2.2.2]octane, and in the presence of a diluent,such as, for example, toluene, xylene or chlorobenzene, at temperaturesbetween 80° C. and 150° C., and the volatile components are, after thereaction has ended, distilled off under reduced pressure.

The formula (IV) provides a general definition of the substitutedaminoazines to be used as starting materials in the process (b)according to the invention for preparing the compounds of the formula(I). In the formula (IV), A, R¹ and R² each preferably or in particularhave those meanings which have already been mentioned above, inconnection with the description of the compounds of the formula (I), asbeing preferred or as being particularly preferred for A, R¹ and R²; Zpreferably represents fluorine, chlorine, bromine, C₁–C₄-alkoxy orphenoxy, in particular, chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (IV) are known and/or can beprepared by processes known per se (cf. U.S. Pat. No. 4,690,707, DE 19501 174).

The formula (V) provides a general definition of the thiophenederivatives further to be used as starting materials in the process (b)according to the invention. In the formula (V), Q, R⁴ and R⁵ eachpreferably or in particular have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe formula (I), as being preferred or as being particularly preferredfor Q, R⁴ and R⁵.

The starting materials of the formula (V) are known and/or can beprepared by processes known per se (cf. EP 30 142/U.S. Pat. No.4,481,029/U.S. Pat. No. 4,599,103/U.S. Pat. No. 4,701,535, PreparationExamples).

The formula (VI) provides a general definition of the substitutedthiophene derivatives to be used as starting materials in the process(c) according to the invention for preparing the compounds of theformula (I). In the formula (VI), Q, R⁴ and R⁵ each preferably or inparticular have those meanings which have already been mentioned above,in connection with the description of the compounds of the formula (I),as being preferred or as being particularly preferred for Q, R⁴ and R⁵;Z preferably represents fluorine, chlorine, bromine, C₁–C₄-alkoxy orphenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (VI) are known and/or can beprepared by processes known per se.

The formula (VIII) provides a general definition of the substitutedaminothiophenes to be used as starting materials in the process (d)according to the invention for preparing compounds of the generalformula (I). In the general formula (VIII), R⁴ and R⁵ each preferably orin particular have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred or asbeing particularly preferred for R⁴ and R⁵.

The starting materials of the general formula (VIII) are known and/orcan be prepared by processes known per se (cf. Aust. J. Chem. 48 (1995),1907–1916).

Suitable diluents for carrying out the processes (a), (b), (c) and (d)according to the invention are especially inert organic solvents. Theseinclude, in particular, aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as, for example, benzine, benzene,toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride;ethers, such as diethyl ether, diisopropyl ether, dioxane,tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycoldiethyl ether; ketones, such as acetone, butanone or methyl isobutylketone; nitrites, such as acetonitrile, propionitrile or benzonitrile;amides, such as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorictriamide; esters, such as methyl acetate or ethyl acetate, andsulphoxides, such as dimethyl sulphoxide.

The processes (a), (b), (c) and (d) according to the invention arepreferably carried out in the presence of a suitable reaction auxiliary.Suitable reaction auxiliaries are all customary inorganic or organicbases. These include, for example, alkaline earth metal or alkali metalhydrides, hydroxides, amides, alkoxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydride, sodium amide, sodiummethoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide,potassium hydroxide, ammonium hydroxide, sodium acetate, potassiumacetate, calcium acetate, ammonium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate or ammoniumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the processes (a), (b), (c) and (d) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween −20° C. and +150° C., preferably between −10° C. and +120° C.

The processes (a), (b), (c) and (d) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to carry out the processes according to the invention underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

For carrying out the processes (a), (b), (c) and (d) according to theinvention, the starting materials are generally employed inapproximately equimolar amounts. However, it is also possible to use arelatively large excess of one of the components. The reaction isgenerally carried out in a suitable diluent in the presence of areaction auxiliary, and the reaction mixture is generally stirred at therequired temperature for several hours. Work-up is carried out bycustomary methods (cf. the Preparation Examples).

If appropriate, salts can be prepared from the compounds of the generalformula (I) according to the invention. Such salts are obtained in asimple manner by customary methods for forming salts, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, methylene chloride, acetone, tert-butylmethyl ether or toluene, and adding a suitable base. The salts canthen—if appropriate after prolonged stirring—be isolated byconcentration or filtering off with suction.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and railway tracks, and on paths and squares with orwithout tree plantings. Equally, the active compounds according to theinvention can be employed for the control of weeds in perennial crops,for example forests, decorative tree plantings, orchards, vineyards,citrus groves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, in lawns, turf andpasture-land, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when used on the soiland on above-ground parts of plants. To a certain extent, they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothpre-emergence and post-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially the following: aromatics, such as xylene,toluene or alkylnaphthalenes, chlorinated aromatics and chlorinatedaliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes ormethylene chloride, aliphatic hydrocarbons, such as cyclohexane orparaffins, for example petroleum fractions, mineral and vegetable oils,alcohols, such as butanol or glycol and also their ethers and esters,ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifying and/or foam-forming agents are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as protein hydrolysates; suitable dispersing agents are: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For the control of weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop-(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate,flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl,-sodium), flurenol(-butyl), fluridone, fluroxypyr(-methyl),flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop-(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfiron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propisochlor,propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl),rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb,tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl),triclopyr, tridiphane, trifluralin and triflusulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples below.

PREPARATION EXAMPLES Example 1

0.75 g (2,9 mmol) of2-phenoxycarbonylamino-4-methoxy-6-methyl-1,3,5-triazine is dissolved in40 ml of acetonitrile and admixed successively with 0.75 g (3,2 mmol) ofmethyl 2-methyl-3-sulphamoyl-thiophene-4-carboxylate and 0.49 g (3.2mmol) of diazabicycloundecene (DBU). The reaction mixture is stirred atroom temperature (about 20° C.) for 12 hours and then concentrated underwater-pump vacuum. The residue is taken up in methylene chloride and themixture is washed with 2N hydrochloric acid and with water, dried withmagnesium sulphate and filtered. The filtrate is concentrated underwater-pump vacuum, the residue is digested with diethyl ether and theresulting crystalline product is isolated by filtration with suction.

This gives 0.60 g (52% of theory) ofN-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(4-methoxycarbonyl-2-methyl-thien-3-yl-sulphonyl)-ureaof melting point 195° C.

Example 2

1.05 g (7.5 mmol) of chlorosulphonyl isocyanate are initially charged in75 ml of methylene chloride. After cooling to −10° C., a solution of1.16 g (7.5 mmol) of 2-amino-4,6-dimethoxy-pyrimidine in 30 ml ofmethylene chloride is added dropwise with stirring to this mixture, andthe mixture is stirred at −10° C. for 30 minutes. At 0° C., a solutionof 1.28 g (7.5 mmol) of methyl 3-amino-2-methyl-thiophene-4-carboxylateand 0.75 g (7.5 mmol) of triethylamine in 50 ml of methylene chloride isthen added dropwise, and the reaction mixture is stirred at roomtemperature (about 20° C.) for 12 hours. 100 ml of water in 100 ml of 2Nhydrochloric acid are then added and the organic phase is separated off,washed with 50 ml of water, dried with magnesium sulphate and filtered.The filtrate is concentrated under water-pump vacuum and the residue iscrystallized from ethanol.

This gives 2.1 g (66% of theory) ofN-(4,6-dimethoxy-pyrimidin-2-yl)-N′-(4-methoxycarbonyl-2-methyl-thien-3-yl-amino-sulphonyl)-ureaof melting point 174° C.

Analogously to Examples 1 and 2, and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to prepare, for example, the compounds of the generalformula (I) listed in Table 1 below.

TABLE 1 Examples of the compounds of the formula (I) (I)

Melting Ex. point No. A Q R¹ R² R³ R⁴ R⁵ (° C.) 3 CH NH OCH₃ OCH₃ Hn-C₃H₇ C₂H₅ 140 4 CH NH OCH₃ OCH₃ H i-C₃H₇ C₂H₅ 154 5 CH NH OCH₃ OCH₃ HC₂H₅ CH₃ 195 6 CH — OCH₃ OCH₃ H CH₃ CH₃ 194Starting Materials of the Formula (V):

Example (V-1)

Step 1

At from 0° C. to 5° C., a solution of 19.9 g (0.29 mol) of sodiumnitrite in 60 ml of water is added dropwise with stirring to a solutionof 42.7 g (0.25 mol) of methyl 3-amino-2-methyl-thiophene-4-carboxylatein 75 ml of 10% strength aqueous hydrochloric acid. The reaction mixtureis stirred at from 0° C. to 5° C. for 60 minutes. The excess of nitriteis subsequently destroyed using amidosulphonic acid. At from 0° C. to 5°C., the mixture is then added dropwise with stirring to a solution of 35g (0.55 mol) of sulphur dioxide in 300 ml of methylene chloride. Afteraddition of 1.5 g of copper(I) chloride and 1.5 g ofdodecyl-trimethylammonium bromide, the reaction mixture is stirred at40° C. for 60 minutes and then at 20° C. for 12 hours. 18 ml of 35%strength aqueous hydrochloric acid are then added, the mixture isstirred at 20° C. for 4 hours and the phases are then separated. Theaqueous phase is re-extracted with methylene chloride and the combinedorganic phases are washed with water, dried with magnesium sulphate andfiltered. The filtrate is concentrated under water-pump vacuum and theresidue is crystallized from hexane.

This gives 51.7 g (81% of theory) of4-methoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride.

Step 2

A mixture of 45 g (177 mmol) of4-methoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride, 34 g (354mmol) of ammonium carbonate and 400 ml of methylene chloride is stirredat room temperature (about 20° C.) for 12 hours. The mixture is filteredand the solvent is distilled off from the filtrate under water-pumpvacuum, the residue is digested with diethyl ether and the crystallineproduct is isolated by filtration with suction.

This gives 21.5 g (52% of theory) of4-methoxycarbonyl-2-methyl-thiophene-3-sulphonamide.

USE EXAMPLES Example A

Pre-Emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 1000 litresof water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2,3, 4, 5 and 6 show very strong activity against weeds, and some of themare tolerated well by crop plants, such as, for example, cotton, maizeand soya.

Table A1 Pre-emergence test/greenhouse Active compound of Applicationrate Alope- Ama- Preparation Example No. (g of ai/ha) Cotton curusranthus Stellaria Viola

(6) 15 0 80 90 90 100

TABLE A2 Pre-emergence test/greenhouse Active compound of ApplicationCheno- Matri- Preparation Example No. rate (g of ai/ha) Maize Cyperuspodium caria Viola

(5) 125 20 95 95 100 95

TABLE A3 Pre-emergence test/greenhouse Active compound of ApplicationPreparation Example No. rate (g of ai/ha) Soya Matricaria StellariaVeronica Viola

(1) 4 10 95 95 95 100

TABLE A4 Pre-emergence test/greenhouse Active compound of ApplicationAlope- Ama- Preparation Example No. rate (g of ai/ha) curus Abutilonranthus Sinapis

(3) 250 70 80 90 90

TABLE A5 Pre-emergence test/greenhouse Active compound of ApplicationAlope- Ama- Preparation Example No. rate (g of ai/ha) curus CyperusAbutilon ranthus Sinapis

(4) 250 100 90 95 90 90

TABLE A6 Pre-emergence test/greenhouse Active compound of ApplicationAma- Preparation Example No. rate (g of ai/ha) Maize Cyperus Abutilonranthus Sinapis

(2) 250 20 95 90 95 95

Example B

Post-Emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5–15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen so that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2, 5and 6 exhibit very strong activity against weeds, and some of them aretolerated well by crop plants, such as, for example, barley and wheat.

TABLE B1 Post-emergence test/greenhouse Active compound of ApplicationAlope- Echino- Abu- Stel- Vero- Preparation Example No. rate (g ofai/ha) curus chloa Lolium tilon laria nica Viola

(1) 15 100 100 100 100 100 100 100

TABLE B2 Post-emergence test/greenhouse Active compound of ApplicationAma- Preparation Example No. rate (g of ai/ha) Barley AlopecurusAbutilon ranthus Stellaria

(6) 4 20 90 100 100 95

TABLE B3 Post-emergence test/greenhouse Active compound of ApplicationAma- Matri- Xan- Preparation Example No. rate (g of ai/ha) Wheat ranthuscaria Viola thium

(2) 125 0 100 100 100 95

TABLE B4 Post-emergence test/greenhouse Active compound of ApplicationCheno- Ipo- Matri- Preparation Example No. rate (g of ai/ha) WheatSetaria podium moea caria

(5) 125 20 90 100 100 100

1. A compound selected from the group consisting of a compound of theFormula (I)

wherein A represents a CH grouping, Q represents a single bond orrepresents NH, R¹ represents hydrogen, halogen with the exception ofiodine, or in each case optionally substituted alkyl, alkoxy, alkylthio,alkylamino, dialkylamino, aryloxy or heterocyclyloxy, R² representshydrogen, halogen with the exception of iodine, or in each caseoptionally substituted alkyl, alkoxy, alkylthio, alkylamino,dialkylamino, aryloxy or heterocyclyloxy, R³ represents hydrogen oroptionally substituted alkyl, R⁴ represents halogen or optionallysubstituted alkyl and—if Q represents NH—also represents hydrogen, andR⁵ represents hydrogen or in each case optionally substituted alkyl,alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl or heterocyclyl, and asalt of the compound of the Formula (I).
 2. The compound according toclaim 1, wherein R¹ represents hydrogen, represents halogen with theexception of iodine, represents in each case optionally cyano-, halogen-or C₁–C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino ordialkylamino having in each case 1 to 4 carbon atoms in the alkylgroups, or represents in each case optionally cyano-, halogen-,C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted phenoxy, oxetanyloxy, furyloxyor tetrahydrofuryloxy, R² represents hydrogen, represents halogen withthe exception of iodine, represents in each case optionally cyano-,halogen- or C₁–C₄-alkoxy-substituted alkyl, alkoxy, alkylthio,alkylamino or dialkylamino having in each case 1 to 4 carbon atoms inthe alkyl groups, or represents in each case optionally cyano-,halogen-, C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted phenoxy, oxetanyloxy,furyloxy or tetrahydrofuryloxy, R³ represents hydrogen or representsoptionally C₁–C₄-alkoxy-, C₁–C₄-alkyl-carbonyl- orC₁–C₄-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms, R⁴represents optionally cyano-, halogen- or C₁–C₄-alkoxy-substituted alkylhaving 1 to 6 carbon atoms and—if Q represents NH—also representshydrogen, and R⁵ represents hydrogen, represents optionally cyano-,halogen- or C₁–C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally halogen-substituted alkenyl oralkinyl having in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁–C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally 1 to 4 carbon atoms in the alkylmoiety, or represents in each case optionally cyano-, halogen-,C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted oxetanyl, furyl ortetrahydrofuryl.
 3. The compound according to claim 1, wherein R¹represents hydrogen, fluorine, chlorine, bromine, or represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino,ethyl-amino, n- or i-propylamino, dimethylamino or diethylamino, R²represents fluorine, chlorine, bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,methyl-thio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n-or i-propylamino, dimethylamino or diethylamino, R³ represents hydrogenor represents in each case optionally methoxy-, ethoxy-, n- ori-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxy-carbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl, R⁴represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, and R⁵ represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
 4. The compoundaccording to claim 1, wherein R¹ represents hydrogen, fluorine,chlorine, bromine, represents in each case optionally fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy,ethoxy, methylthio, ethylthio, methylamino, ethylamino, or representsdimethylamino, R² represents fluorine, chlorine, bromine, represents ineach case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylthio,ethylthio, methylamino or ethyl-amino, or represents dimethylamino, R³represents hydrogen or methyl, R⁴ represents in each case optionallyfluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, and R⁵represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in eachcase optionally fluorine- or chlorine-substituted propenyl or propinyl.5. The compound of claim 1, wherein said compound is a salt of saidcompound of the Formula I and said salt is selected from the groupconsisting of a sodium, potassium, magnesium, calcium, ammonium,C₁–C₄-alkyl-ammonium, di-(C₁–C₄-alkyl)-ammonium,tri-(C₁–C₄-alkyl)-ammonium, tetra-(C₁–C₄-alkyl)-ammonium,tri-(C₁–C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium anddi-(C₁–C₂-alkyl)-benzyl-ammonium salt of said compound according toclaim
 1. 6. A process for preparing a compound according to claim 1,selected from the group consisting of processes (a), (b), (c) and (d),wherein (a) said process (a) comprises the step of reacting anaminoazine of the Formula (II)

wherein A, R¹ and R² are each as defined in claim 1 with athienyl(amino)sulphonyl isocyanate of the Formula (III)

wherein Q, R⁴ and R⁵ are each as defined in claim 1, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, (b) said process (b) comprises the step of reacting asubstituted aminoazine of the Formula (IV)

wherein A, R¹ and R² are each as defined in claim 1, Z representshalogen, alkoxy or aryloxy and R has the meaning given for R³ in claim 1or represents the grouping —C(O)—Z, with a thiophene derivative of theFormula (V)

wherein Q, R⁴ and R⁵ are each as defined in claim 1, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, (c) said process (c) comprises the step of reacting anaminoazine of the Formula (II)

wherein A, R¹ and R² are each as defined in claim 1, with a thiophenederivative of the Formula (VI)

wherein Q, R⁴ and R⁵ are each as defined in claim 1 and Z representshalogen, alkoxy or aryloxy, optionally in the presence of a reactionauxiliary and optionally in the presence of a diluent, (d) said process(d) comprises the steps of reacting an aminoazine of the Formula (II)

wherein A, R¹ and R² are each as defined in claim 1, with achlorosulphonyl isocyanate, optionally in the presence of a diluent, andreacting a resulting chlorosulphonylaminocarbonylamino-azine of theFormula (VII)

wherein A, R¹ and R² are each as defined in claim 1 wherein saidchlorosulphonylaminocarbonylamino-azine is reacted either afterintermediate isolation or “in situ” with a substituted aminothiophene ofthe Formula (VIII)

wherein R⁴ and R⁵ are each as defined in claim 1, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, each of said processes (a), (b), (c) or (d) respectively,optionally further comprising the step of converting the compoundobtained by each of said respective process into a salt.
 7. A method forcontrolling undesirable vegetation, comprising the step of allowing oneor more of the compounds according to claim 1 to act on a memberselected from the group consisting of one or more undesirable plants, ahabitat of said undesirable plants, and combinations thereof.
 8. Aherbicidal composition, comprising a compound according to claim 1 and amember selected from the group consisting of one or more extenders, oneor more surfactants and combinations thereof.